Island Hopping in Greece

The most popular way to travel between the islands is by ferry as there are multiple ferry routes available daily that can be convenient for your schedule and budget friendly.  You can reach most of the Greek Islands in about 30 minutes on a fast ferry where you can also bring your rental car or motorbike if you have one.  Don’t worry about renting transportation before you head to the islands as there are several options available, depending on which islands you chose to visit. You can also fly between some of the larger islands which is convenient if there’s an airport on the island you are visiting and you are planning to stay for a while. 

There’s also the option to book a Greek island-hopping cruise on a variety of cruise lines that will pick you up from the port in Piraeus (just outside of Athens) with an itinerary for specific islands you will visit daily.  Some of these cruise lines will be at port late into the evening so you are able to immerse yourself into the island for a full day and evening before heading back to your ship for dinner, shows and dancing and then wake up the next morning at another island. 

On my island-hopping adventure in September, I visited four islands while the weather was still in the low 80s, with sunny clear skies and the prime time for dining outdoors and enjoying an ice-cold cocktail while soaking in the views.

One of the entrances into Old Town Rhodes

Rhodes, Greece

We spent a large portion of the day in Rhodes Old Town, where we adored the pebbled streets that you get lost in while admiring the castle walls.  The Old Town of Rhodes was declared the World Heritage Site by UNESCO in 1988 and is the largest medieval city in all of Europe.  Just outside of the city you can watch super yachts and cruise ships anchor for the day.  As you walk through the streets, you will hear church bells ringing while you follow your nose to the smell of gelato being served through narrow streets.  There are endless opportunities to purchase handmade leather sandals, beautiful handbags, silk and lace clothing, wooden bowls and utensils, local baked goods, candy and so much more.  Beware, when you order a beer at a local restaurant, it will likely come in a glass the size of a boot! I still cannot get over how adorable this ancient little town is and highly recommend it as a must do when in Rhodes. 

Fishing boats docked in Heraklion

Heraklion, Crete

Heraklion, Crete is a beautiful seaside town where you can watch sailboats come in and out, fisherman reel fish and sell them at the market on the street and stroll through shops and restaurants. We grabbed a snack at a market and sat seaside watching boats come and go and then walked down by the beach where we found a little restaurant while we enjoyed grilled vegetables and souvlaki by the sea. Shops are lined with handmade wooden utensils and beautiful glass lanterns.  You can also find brands you might recognize nestled into the neighborhood.

Donkeys bringing tourists up the caldera in Santorini

Santorini, Greece

As you walk the streets in Santorini, you’ll admire everything from the bright white buildings with vibrant flowers and trees nestled between the cobblestone streets, restaurants in the cliffside with spectacular views, cool ocean vibes and music. There are fresh fish on ice, woodfire cooking and lots of sparkling wine.  You can catch a very affordable bus to Oia to enjoy the sunset and admire the bright blue rooftops you see in all of the pictures. If you take a bus, be patient knowing that it will arrive even if it’s slightly late, but it’s a great way to get around town. You can also rent ATVs, 4-wheelers, mopeds and scooters to get around Santorini. This is definitely a place you will want to spend several days exploring as there’s just too much to see and do in a short period of time. 

If you are arriving by cruise ship, there’s the famous Donkey Trail which used to be the only way to get from the ocean to the top of Santorini where you can either walk the trail or ride a donkey. There are not spots to stop and rest in the shade and it is quite a long physical journey. Once you start, there’s no way to change your mind mid-way.  I rode the cable car one way and walked the Donkey Trail the other, but did not ride the donkeys.  

The brightly colored doors of Mykonos

Mykonos, Greece

Mykonos was much better than I’d imagined with crisp white buildings like Santorini and beautiful walking paths between with big stones lined with white stucco, bright vibrant trees and flowers, colorful high-end shops, restaurants with glass lanterns blowing in the breeze.  The entire island has a boho-chic vibe just screaming for you to spend a few days in a swanky hotel and enjoy the seaside nightlife.  You can watch local fisherman catch and filet fish on the beach, tiny little boats floating in water so crisp it looks like a mirror.  The shopping is just amazing with beautiful dresses, unique men’s swimwear, sunglasses and sandals, straw bags and designer brands throughout the island.  Keep walking in the capital town of Hora and you will find yourself on a tiny sidewalk surrounded by restaurants and waves crashing up at your feet.  Cool music, trendy cocktails and food are everywhere you look.  We stopped for a snack at one of these restaurants on the water with a group of people we’d met and ordered sharable risotto, muscles, clams and saganaki (Greek fried cheese).  If you’ve not been to Mykonos you must add this to your list of places to spend a few days!

We can help you plan your island-hopping adventure! Contact one of our travel specialists today.